Process of oxidizing compounds and producing terpene peroxid.



A. s. RAMAGE. PROCESS. OF OXIDIZING COMPOUNDS AND PRODUCING TERPENEPEROXID.

I APPLICATION FILED MAR. 6, 1906. 1,0919 39, Patented May 26, 1914.

Wzznesses: 3 Irv/0621602".-

WMM 7 awm UNITED STATES PATENT oEEIoE.

ALEXANDER S. RAMAGE, OF DETROIT, MICHIGAN, ASSIGNOR TO EUGENE A. BYRNESAND CLINTON PAUL TOWNSEND, OF WASHINGTON, DISTRICT OF COLUMBIA.

PROCESS OF OXIDIZING COMPOUNDS AND. PRODUCING TERPENE PEROXID.

Specification of Letters Patent.

Patented May 26, 1914.

Application filed March 6, 1906. Serial No. 304,587.

Detroit, in the county of Wayne and State of Michigan, have inventedcertain new and useful Improvements 1n Processes of Oxidizing Compoundsand Producing Terpene.

Peroxid, of which the following is a specification.

In my U. S. Patent 710,893, granted October 7, 1902, I have describedand claimed a chemical compound termed terpene peroxid, produced b; theoxidation of a terpene compound, such, for instance, as cineol. Thiscompound has heretofore been produced by heating cineol to about 60 C.and causing ozonized air to bubble through it, the peroxid thenappearing in dense, white fumes and being condensed and collected as aliquid in a separate vessel. I have now discovered that the oxidation ofthe .terpene hydrocarbon may be effected more rapidly and completely bysubjecting the vaporized hydrocarbon to the action of ozone or ozonizedair in the presence of a catalytic agent, especially platinum black.

A suitable apparatus for carrying out the process is shown in theaccompanying drawing, in which the figure is a longitudinal verticalsection showing the ozonizer and collecting vessels in elevation.

The apparatus illustrated comprises a vessel 1 supported in an oil bath2 heated by a steam coil 3. The vessel 1 has a supply pipe 4 whichextends below the'surface 5 of the terpene hydrocarbon and preferably toa point near the bottom of the vessel.

6 is an air-inlet pipe communicating with a suitable blower or source,of air under pressure, not shown, and having its open end extending to apoint near the bottom of the vessel 1; a valve 7 serves to regulate theair supply. The outlet pipe 8 from the vessel 1 opens into acatch-vessel 12 from which a pipe 13 opens into a horizontal chamber 14containing a catalytic agent 15, preferably platinized asbestos. A pipe16 leads direct from-the discharge aperture 9 of an ozonizer 10 to thereceiving end of the chamber 14.

11 represents the air-inlet to the ozonizer 10. A delivery pipe 17extends from the other end of this chamber to the first of a series ofcollecting vessels 18, 19, 2Q arranged at successively increasingheights and connected by pipes 21,22.

In employing this apparatus, the cineol or other liquid to be oxidizedis placed in. the vessel 1 and air is forced through it by means of thepipe 6. For the oxidation of cineol the liquid in the vessel 1 ispreferably heated to a temperature exceeding 100 0., for which purpose asteam pressure of about 100 pounds may be maintained in the coil 3. Thevapor of the liquid, together with the particles of liquid mechanicallyconveyed by the current of air, passes through the catch-vessel 12,where entrained liquid deposits, and thence through the platinizedasbestos 15 wherein it is subjected to the action of ozone suppliedthrough the pipe 16. The peroxid fumes or other product pass thence intothe vessel 18 where a large proportion is condensed and subsides as aliquid, the remainder bein displaced into the collecting vessels above.The liquid product is recovered from the three vessels. It is found thatthe arrangement of these'vessels in cascade materially facilitates thesubsidence of the fumes, on account of the height and the cooling eifectof the connecting tubes 21, 22

through which the fumes rise.

I claim 1. The process of oxidizing liquid compounds, the vapors ofwhich are oxidizable by ozone in the presence of a catalytic agent,which consists in first vaporizing the liquid and then passing the vaporin contact with a catalytic agent and simultaneously subjecting it tothe action of ozone, substantially as described.

2. The process of oxidizing liquid organic compounds, the vapors ofwhich are oxidizable by ozone in the presence of a catalytic agent,which consists in first vaporizing the liquid and then passing the vaporin contact with a catalytic agent and simultaneously subjecting it tothe action of ozone, substantially as described.

3. The process of oxidizing terpene compounds, which consists in passingthe vapor of a terpene in contact with-a catalytic agent andsimultaneouslysubjecting it to the action of ozone, substantially asdescribed.

4. The process of oxidizing terpene compounds, which consists in passingthe vapor of a terpene in contact, with platinized asbestos andsimultaneously subjecting it to the action of ozone, substantially asdescribed.

5. The process of oxidizing terpene compounds, which consists insuccessively vaporizing a terpene by a current of air, and reacting onthe mixture of terpene vapor and air with an oxidizing agent, in thepresence of a catalytic agent, substantially as described.

6'. The process of oxidizing terpene compounds, which consists insuccessively vaporizing a terpene by a current of air, at a temperatureabove 100 0., and reacting on the mixture of terpene vapor and air withan oxidizing agent, in the presence of a catalytic agent, substantiallyas described.

7 The process of oxidizing terpene compounds, Which consists invaporizing a terpeneby a current of air, passing the vapor in contactwith a catalytic agent, and simultaneously subjecting it to the actionof ozone, substantlally as described.

8. The process of oxidizing terpene ,compounds, which consists invaporizing a terpene by a current of air, at a temperature above 100 0.,passing the vapor in contact with a catalytic agent, and simultaneouslysubjecting it to the action of ozone, substantially as described.

9. The process which consists in oxidizing a terpene and causing theresulting fumes to subside decrementally at successively increasingelevations, substantially as described.

10. The process which consists in oxidizing a terpene by thesimultaneous action of a catalytic agent and ozone, and causin theresulting fumesto subside in separate 0 ambers at successivelyincreasing elevations, substantially as described.

In testimony whereof, I aflix my signature in presence of two witnesses.

' ALEXANDER S. RAMAGE. Witnesses:

ALVA L. Bu'rz, JONATHAN PALMER, Jr.

